Scaffold Editing of Cubanes into Homocubanes, Homocuneanes via Cuneanes

Abstract

The selective synthesis of cage-type hydrocarbons through the editing of the highly symmetric molecule cubane can be anticipated as one of the efficient approaches. In this paper, we identify a catalyst that facilitates the efficient scaffold isomerization of cubanes into homocubanes. This approach, which involves the direct synthesis of homocubanol esters, is promising as a novel method for the synthesis of phenoxy bioisosteres. Additionally, we observed that the isomerization of 1, 4-bis(acyloxymethl)cubane results in the generation of both 𝘋₂- and 𝘊₂-symmetrical bishomocubanes. The same catalyst was also applied to the isomerization of acyloxymethylcuneanes, producing homocuneanol esters.